As regards a partial hydrogenation reaction for producing an alkene compound from an alkyne compound, studies using a catalyst of a transition metal such as palladium or nickel have been conducted. For example, H. Lindlar reported that an alkyne compound was partially hydrogenated in the presence of a catalyst prepared by poisoning palladium carried on calcium carbonate with lead acetate to produce a cis-alkene compound with high selectivity. At present, this catalyst is most widely used as a catalyst combining a high activity and high cis-selectivity.
The present inventors have disclosed that some phosphine-palladium complexes are useful as catalysts for partially hydrogenating alkyne compounds with high activity. For example, Patent Document 1 discloses a process of producing an alkene compound including partially hydrogenating an alkyne compound, which is a reaction substrate, using a catalytic amount of 1,2-bis(diphenylphosphino)propane palladium chloride as a phosphine-palladium complex in a mixed solvent of N,N-dimethylformamide (DMF) and an alcohol in the presence of potassium tert-butoxide or sodium borohydride and in the presence of hydrogen (for example, Japanese Unexamined Patent Application Publication No. 2003-236386).
Furthermore, in Journal of Catalysis, Vol. 194, pp. 146-152 (2000), a hydrogenation reaction of an alkyne compound using palladium nanoparticles carried on montmorillonite as a catalyst has been reported. Specifically, the following example has been reported: A hydrogenation reaction of 1-phenyl-1-butyne was conducted using the above palladium nanoparticles as a catalyst at room temperature in THF. As a result, at a reaction time of 60 minutes, 1-phenyl-cis-butene was produced in an amount of about 60%, 1-phenyl-trans-butene was produced in an amount of about 30%, and 1-phenylbutane was produced in an amount of about 10%.